Cheff became the head coach at Lewis–Clark State College since 1977, winning 16 National Association of Intercollegiate Athletics (NAIA) titles. 114 of his former players have gone on to play professionally, with 14 reaching Major League Baseball. Cheff was named NAIA coach of the year eight times. He was inducted into the NAIA Hall of Fame in 1994 and the American Baseball Coaches Association (ABCA) Hall of Fame in 2006. He won the ABCA's Lefty Grove Award, given for lifetime achievement to amateur baseball. He has been a coach with the United States national baseball team (1991, 1994) and has managed the Alaska Goldpanners and Anchorage Bucs in the Alaska Baseball League.
Cheff and his wife, Karen, a retired elementary school teacher, have three sons: Trever, Tyler, Toby.